DE69901656T2 - 1,2,4-Triazin Derivat, dessen Herstellung und dessen Verwendung als Referenzmarker um die Reinheit und Stabilität von "Lamotrigin" zu bestimmen - Google Patents
1,2,4-Triazin Derivat, dessen Herstellung und dessen Verwendung als Referenzmarker um die Reinheit und Stabilität von "Lamotrigin" zu bestimmenInfo
- Publication number
- DE69901656T2 DE69901656T2 DE69901656T DE69901656T DE69901656T2 DE 69901656 T2 DE69901656 T2 DE 69901656T2 DE 69901656 T DE69901656 T DE 69901656T DE 69901656 T DE69901656 T DE 69901656T DE 69901656 T2 DE69901656 T2 DE 69901656T2
- Authority
- DE
- Germany
- Prior art keywords
- lamotrigine
- sample
- solution
- compound
- purity
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- PYZRQGJRPPTADH-UHFFFAOYSA-N lamotrigine Chemical compound NC1=NC(N)=NN=C1C1=CC=CC(Cl)=C1Cl PYZRQGJRPPTADH-UHFFFAOYSA-N 0.000 title claims description 51
- 229960001848 lamotrigine Drugs 0.000 title claims description 50
- 239000003550 marker Substances 0.000 title claims description 16
- 238000002360 preparation method Methods 0.000 title description 10
- 150000003920 1,2,4-triazines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 46
- 239000000243 solution Substances 0.000 claims description 38
- 239000000523 sample Substances 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 15
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 14
- 238000012360 testing method Methods 0.000 claims description 12
- 238000004809 thin layer chromatography Methods 0.000 claims description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
- RDUGDEWOUWFKPL-UHFFFAOYSA-N n-[5-amino-6-(2,3-dichlorophenyl)-1,2,4-triazin-3-yl]-2,3-dichlorobenzamide Chemical compound N=1N=C(C=2C(=C(Cl)C=CC=2)Cl)C(N)=NC=1NC(=O)C1=CC=CC(Cl)=C1Cl RDUGDEWOUWFKPL-UHFFFAOYSA-N 0.000 claims description 9
- 239000002552 dosage form Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 239000012086 standard solution Substances 0.000 claims description 8
- 238000010992 reflux Methods 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 239000012488 sample solution Substances 0.000 claims description 6
- FIBBFBXFASKAON-UHFFFAOYSA-N 2,3-dichlorobenzoyl cyanide Chemical compound ClC1=CC=CC(C(=O)C#N)=C1Cl FIBBFBXFASKAON-UHFFFAOYSA-N 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- OTXHZHQQWQTQMW-UHFFFAOYSA-N (diaminomethylideneamino)azanium;hydrogen carbonate Chemical compound OC([O-])=O.N[NH2+]C(N)=N OTXHZHQQWQTQMW-UHFFFAOYSA-N 0.000 claims description 4
- YBONBWJSFMTXLE-UHFFFAOYSA-N 2,3-dichlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC(Cl)=C1Cl YBONBWJSFMTXLE-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 238000011835 investigation Methods 0.000 claims 1
- 239000012535 impurity Substances 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000007787 solid Substances 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 7
- 239000008186 active pharmaceutical agent Substances 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 229940088679 drug related substance Drugs 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 229940079593 drug Drugs 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000008194 pharmaceutical composition Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 230000001105 regulatory effect Effects 0.000 description 4
- 238000007086 side reaction Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 229940126062 Compound A Drugs 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 229940126534 drug product Drugs 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- OVNGWOHWYFBGKF-UHFFFAOYSA-N 3-amino-6-(2,3-dichlorophenyl)-2h-1,2,4-triazin-5-one Chemical compound OC1=NC(N)=NN=C1C1=CC=CC(Cl)=C1Cl OVNGWOHWYFBGKF-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 238000000451 chemical ionisation Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000007857 degradation product Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000013074 reference sample Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000012085 test solution Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- BXDSJOGMJUKSAE-CHHVJCJISA-N (1e)-2,3-dichloro-n-(diaminomethylideneamino)benzenecarboximidoyl cyanide Chemical compound NC(N)=N\N=C(\C#N)C1=CC=CC(Cl)=C1Cl BXDSJOGMJUKSAE-CHHVJCJISA-N 0.000 description 1
- GKNCZOMKFQSLCL-WYMPLXKRSA-N (1z)-2,3-dichloro-n-[[n'-(2,3-dichlorobenzoyl)carbamimidoyl]amino]benzenecarboximidoyl cyanide Chemical compound C=1C=CC(Cl)=C(Cl)C=1C(=O)N=C(N)N\N=C(/C#N)C1=CC=CC(Cl)=C1Cl GKNCZOMKFQSLCL-WYMPLXKRSA-N 0.000 description 1
- PQQZYNVQDUZLTQ-UHFFFAOYSA-N (2,3-dichlorobenzoyl) 2,3-dichlorobenzoate Chemical compound ClC1=CC=CC(C(=O)OC(=O)C=2C(=C(Cl)C=CC=2)Cl)=C1Cl PQQZYNVQDUZLTQ-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- 241000557626 Corvus corax Species 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 238000012863 analytical testing Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229940126585 therapeutic drug Drugs 0.000 description 1
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/15—Medicinal preparations ; Physical properties thereof, e.g. dissolubility
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
- C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
- C07D253/07—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members with hetero atoms, or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D253/075—Two hetero atoms, in positions 3 and 5
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/90—Plate chromatography, e.g. thin layer or paper chromatography
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/10—Composition for standardization, calibration, simulation, stabilization, preparation or preservation; processes of use in preparation for chemical testing
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/14—Heterocyclic carbon compound [i.e., O, S, N, Se, Te, as only ring hetero atom]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/14—Heterocyclic carbon compound [i.e., O, S, N, Se, Te, as only ring hetero atom]
- Y10T436/145555—Hetero-N
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/14—Heterocyclic carbon compound [i.e., O, S, N, Se, Te, as only ring hetero atom]
- Y10T436/145555—Hetero-N
- Y10T436/147777—Plural nitrogen in the same ring [e.g., barbituates, creatinine, etc.]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmacology & Pharmacy (AREA)
- Food Science & Technology (AREA)
- Medicinal Chemistry (AREA)
- Physics & Mathematics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Plural Heterocyclic Compounds (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB9812413.4A GB9812413D0 (en) | 1998-06-10 | 1998-06-10 | Compound and its use |
Publications (2)
Publication Number | Publication Date |
---|---|
DE69901656D1 DE69901656D1 (de) | 2002-07-11 |
DE69901656T2 true DE69901656T2 (de) | 2003-01-30 |
Family
ID=10833464
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE69901656T Expired - Fee Related DE69901656T2 (de) | 1998-06-10 | 1999-03-10 | 1,2,4-Triazin Derivat, dessen Herstellung und dessen Verwendung als Referenzmarker um die Reinheit und Stabilität von "Lamotrigin" zu bestimmen |
Country Status (31)
Country | Link |
---|---|
US (1) | US6333198B1 (fr) |
EP (2) | EP0963980B1 (fr) |
JP (1) | JP2989189B1 (fr) |
KR (1) | KR100322354B1 (fr) |
CN (2) | CN1238454A (fr) |
AP (3) | AP0102286A0 (fr) |
AR (1) | AR014074A1 (fr) |
AT (1) | ATE218552T1 (fr) |
AU (1) | AU2031999A (fr) |
BR (1) | BR9900984A (fr) |
CA (1) | CA2265194C (fr) |
DE (1) | DE69901656T2 (fr) |
DK (1) | DK0963980T3 (fr) |
EA (1) | EA000666B1 (fr) |
ES (1) | ES2178342T3 (fr) |
GB (1) | GB9812413D0 (fr) |
HR (1) | HRP990074A2 (fr) |
HU (1) | HUP9900592A3 (fr) |
ID (1) | ID22957A (fr) |
MA (1) | MA24777A1 (fr) |
NO (2) | NO991151L (fr) |
NZ (1) | NZ334590A (fr) |
PE (1) | PE20000332A1 (fr) |
PL (1) | PL331870A1 (fr) |
PT (1) | PT963980E (fr) |
SG (1) | SG85628A1 (fr) |
SI (1) | SI0963980T1 (fr) |
TR (1) | TR199900520A3 (fr) |
UY (1) | UY25946A1 (fr) |
YU (1) | YU12399A (fr) |
ZA (1) | ZA991951B (fr) |
Families Citing this family (92)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20020055177A1 (en) * | 1999-03-10 | 2002-05-09 | Glaxo Wellcome Inc. | Compound and its use |
AU763244B2 (en) * | 2000-01-03 | 2003-07-17 | Rpg Life Sciences Limited | A process for the preparation of 6-(2,3-dichlorophenyl)-1,2,4-triazine-3,5-diamine, commonly known as lamotrigine |
US7335380B2 (en) | 2000-12-29 | 2008-02-26 | Synthon Ip Inc. | Amlodipine free base |
WO2002053541A1 (fr) | 2000-12-29 | 2002-07-11 | Pfizer Limited | Derive d'amide d'amlodipine |
MXPA03005882A (es) | 2000-12-29 | 2005-04-19 | Pfizer Ltd | Derivado amida de amlodipina. |
MXPA03005886A (es) | 2000-12-29 | 2005-04-19 | Pfizer Ltd | Derivado de aspartato de amlodipina como antagonista del canal de calcio. |
US6653481B2 (en) | 2000-12-29 | 2003-11-25 | Synthon Bv | Process for making amlodipine |
WO2002053538A1 (fr) | 2000-12-29 | 2002-07-11 | Pfizer Limited | Fumarate d'amlodipine |
BR0116552A (pt) | 2000-12-29 | 2004-02-03 | Pfizer Ltd | Hemi-maleato de amlodipina, processo, método para o tratamento ou prevenção de angina ou hipertensão, composição farmacêutica, para uso no tratamento e/ou de angina ou da hipertensão |
AT5874U1 (de) | 2000-12-29 | 2003-01-27 | Bioorg Bv | Pharmazeutische zubereitungen enthaltend amlodipinmaleat |
GB2371862B (en) * | 2000-12-29 | 2004-07-14 | Bioorg Bv | Reference standards for determining the purity or stability of amlodipine maleate and processes therefor |
WO2002053542A1 (fr) | 2000-12-29 | 2002-07-11 | Pfizer Limited | Procede de preparation de maleate d'amlodipine |
DE10134980C2 (de) * | 2001-07-17 | 2003-05-28 | Helm Ag | Verfahren zur Herstellung von Lamotrigin |
CA2366521C (fr) | 2001-12-24 | 2007-03-06 | Brantford Chemicals Inc. | Un procede nouveau et efficace de preparation de lamotrigine et d'autres 3,5-diamino-1,2,4-triazines substituees en position 6 |
AU2003235435A1 (en) * | 2002-03-20 | 2003-10-08 | Teva Pharmaceutical Industries Ltd. | Crystalline forms of quetiapine hemifumarate |
HU225667B1 (en) | 2002-09-20 | 2007-05-29 | Richter Gedeon Nyrt | Method for producing high-purity 3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazine |
ES2209639B1 (es) | 2002-10-31 | 2005-08-01 | Vita Cientifica, S.L. | Procedimiento para la obtencion de un compuesto farmaceuticamente activo y obtencion de su intermedio. |
GB2395483A (en) * | 2003-07-03 | 2004-05-26 | Jubilant Organosys Ltd | Crystalline lamotrigine and its monohydrate |
EP1562912A2 (fr) | 2003-08-28 | 2005-08-17 | Teva Pharmaceutical Industries Limited | Procede de preparation de sels calciques de rosuvastatine |
CA2546701C (fr) * | 2003-11-24 | 2010-07-27 | Teva Pharmaceutical Industries Ltd. | Sels d'ammonium cristallins de la rosuvastatine |
WO2005056534A1 (fr) | 2003-12-02 | 2005-06-23 | Teva Pharmaceutical Industries Ltd. | Norme de reference pour la caracterisation de la rosuvastatine |
US7851624B2 (en) * | 2003-12-24 | 2010-12-14 | Teva Pharamaceutical Industries Ltd. | Triol form of rosuvastatin and synthesis of rosuvastatin |
EP1708708A1 (fr) * | 2004-01-30 | 2006-10-11 | Teva Pharmaceutical Industries Ltd. | Polymorphes d'acide sans montelukast |
EP1709002A2 (fr) * | 2004-01-30 | 2006-10-11 | Teva Pharmaceutical Industries Ltd. | Montelukast de sodium polymorphe |
MD2823G2 (ro) * | 2004-02-12 | 2006-05-31 | Институт Химии Академии Наук Молдовы | Procedeu de determinare cantitativă a sclareolului în extractele, obţinute din salvia de muscat |
MXPA06012220A (es) * | 2004-04-21 | 2007-07-18 | Teva Pharma | Procesos para preparar sodio de montelukast. |
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GR68380B (fr) | 1979-06-01 | 1981-12-28 | Wellcome Found | |
EP0021120B1 (fr) | 1979-06-01 | 1983-04-06 | The Wellcome Foundation Limited | Dérivés de la diamino-3,5 triazine-1,2,4, procédé pour la préparation de tels composés et compositions pharmaceutiques les contenant |
GB8613183D0 (en) | 1986-05-30 | 1986-07-02 | Wellcome Found | Triazine salt |
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GB9426448D0 (en) * | 1994-12-30 | 1995-03-01 | Wellcome Found | Process |
GB9512854D0 (en) * | 1995-06-23 | 1995-08-23 | Wellcome Found | Novel formulation |
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